The Revenue Leadership Podcast · 7 May 2026 · From the week of 4 May
E68: Are You UNINVESTABLE? The New GTM Reality | Cassie Young, General Partner @ Primary Venture Partners
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Cassie Young, General Partner at Primary Venture Partners and a former CRO who spent 15 years running go-to-market teams, joins host Kyle Norton to argue that AI is changing go-to-market economics. She says the era of software bloat is ending because inference and compute costs erode the gross margins that once covered operating waste. The episode covers pricing, board expectations, the PRIME framework for justifying GTM tools, centralized AI adoption, and the executive skills and P&L fluency CROs need. The most important argument is that CROs must show direct P&L impact rather than effort.
For founders
- Cassie Young says investors look hard at early gross and net retention because early customers often turn out not to be the ideal customer profile.
- Cassie Young says a burn multiple under one is amazing and up to two is fine for scaled companies, while a seed-stage founder can run a high burn multiple if they have a plan to bring it down.
- Cassie Young says classic point solutions face the most risk in the AI era, so a startup has to accelerate its roadmap fast enough to earn the right to keep compounding.
- Cassie Young says that with inference costs, mispricing is costly in both directions: underpricing pays customers to use the product and overpricing lets competitors take the business.
For revenue leaders
- Cassie Young says boards are done rewarding effort and want to see direct impact on the P&L, so each go-to-market tool should map to productivity, retention, investment efficiency, momentum or expense reduction.
- Cassie Young calls taking your CFO to lunch her number one hack for CROs, so you can learn where the CFO is being questioned and how they think about the function.
- Kyle Norton says his average outbound BDR produced about $10K in closed-won MRR last month (about $120K ARR per person), up from about $3.5K not long ago, which he credits to AI investments.
- Cassie Young says boards want transformation stories and evidence of what the function is doing, not incremental anecdotes, and that CROs should take credit for their work.
- Kyle Norton says he thinks it is crazy that many CROs are on 50/50 plans and prefers little variable compensation so he can think holistically.
What was said 23, most useful first
Software gross margins no longer cushion go-to-market spending because companies now have to pay for inference and compute. Listen
Cassie Young says the GTM bloat era is over: in traditional software, rich gross margins hid waste in operating expenses, but companies advancing their own products now have to invest in inference and compute. She says go-to-market leaders face a reckoning because they can no longer operate the way they used to.
“In a world where companies have to invest in inference and compute because they're advancing their own products, we don't have that luxury anymore.”
Listen to the episode Strategy & market Link to this Report a problem
ARR per employee has risen in every revenue band while go-to-market efficiency metrics have stagnated. Listen
Citing recent Iconiq benchmarks, Cassie Young says ARR per employee has gone up across every revenue band over the past couple of years, while CAC payback and net magic number have been stagnant if not declining. She reads this gap as a sign that headcount efficiency has improved without go-to-market efficiency improving, which she expects to be reckoned with.
“the one number that's gone up into the right across every single revenue band over the past couple of years has been the ARR per employee number”
Listen to the episode Metrics & finance Link to this Report a problem
With AI features carrying inference costs, underpricing means subsidising customers while overpricing hands share to competitors. Listen
Cassie Young says that in software with roughly 80% gross margins, a pricing mistake on one customer was not very consequential. Now every new feature or agent carries inference costs, so pricing becomes a core part of business strategy, which she links to the rise of consumption-based pricing.
“if you charge too little, you are functionally paying customers to use your product.”
Listen to the episode Pricing & packaging Link to this Report a problem
Boards are done rewarding effort, so a CRO needs to articulate a direct hit on the P&L. Listen
Cassie Young says tool adoption and leading indicators such as BDR coverage or connects are fine but not enough, because CROs must get smarter about operating expenses. Her example is a digital deal room that cut a couple of days off the sales cycle, which she says should be translated into a direct annual gain rather than a multi-layer calculation that is too much math for a board.
“I think boards are done rewarding effort and want to see impact.”
Listen to the episode Metrics & finance Link to this Report a problem
Every new go-to-market tool should map to at least one of five outcomes: productivity, retention, investment efficiency, momentum or expense reduction. Listen
Cassie Young calls this the PRIME framework: Productivity (she uses revenue per employee), Retention (net or gross), Investment efficiency (net magic number and CAC payback), Momentum (top-line growth) and Expense reduction. She says not every tool needs all five, but she would not back a go-to-market solution unless it obviously hits at least one, and she offers it as a buyer framework for CROs.
“I won't touch it if it's not obvious to me that it doesn't hit one of those five things”
Listen to the episode Metrics & finance Link to this Report a problem
An average outbound BDR produced about $10K of closed-won MRR (about $120K ARR) in one month, up from about $3.5K earlier, which Kyle Norton credits to AI investments. Listen
Kyle Norton says the BDR organization's productivity has grown drastically with AI, with per-BDR monthly results rising from about $3.5K to about $6K and then $7K before reaching about $10K in closed-won MRR last month, when a lot of things went right. He says the economics now pencil out so well that he is pulling forward headcount hiring from about four months out in his model.
“I think our average outbound BDR last month produced 10K in closed one ARR or to closed one MRR.”
Listen to the episode Sales team, hiring & comp Link to this Report a problem
If competitors gain the same efficiency from AI, they will ship more with more people rather than the same output with fewer. Listen
Kyle Norton argues that efficiency gains are not simply pocketed as cost savings, because competitive pressure changes the outcome. He says that if rivals become equally more effective they will use the gain to expand output, and his own team is growing faster because its CAC payback pencils out.
“They're going to ship more with more people.”
Listen to the episode Strategy & market Link to this Report a problem
For scaled companies, a burn multiple below one is amazing and up to two is fine, while about three is only kind of decent. Listen
Cassie Young defines burn multiple as net cash burn per dollar of net new ARR and says there are tried and true benchmarks for scaled companies. She adds that the context matters, since she often sees founders with high burn multiples in year one at seed on purpose.
“anything less than one is amazing, like up to two is like fine”
Listen to the episode Metrics & finance Link to this Report a problem
Investors scrutinise early gross and net retention because early customers often turn out not to be the ideal customer profile. Listen
Cassie Young says that even early on, investors look at gross and net retention because founders are asserting an ICP and need evidence that they can protect the base. She notes that later-stage boards often split net retention into current ICP and legacy customers, since early customers usually take time to show they were the wrong fit.
“usually what happens is people sign up as early customers and it takes a little while for them to learn that they weren't the right customers.”
Listen to the episode Retention & customer success Link to this Report a problem
Classic point solutions carry the most risk in the AI era, more than DIY builds of full platforms. Listen
Cassie Young says she is sceptical of vibe-coded DIY CRMs, which she thinks will work in mid-market and enterprise until the first major security breach. She sees extreme risk for classic point solutions, and notes that most startups begin as a point solution or wedge, so they must accelerate the product roadmap to avoid being replaced.
“where I think there's extreme risk in that category are like the classical point solutions.”
Listen to the episode Strategy & market Link to this Report a problem
Go-to-market AI maturity runs from individuals using AI, to centralized standardization, to using AI to create alpha, and most teams sit at the first two levels. Listen
Cassie Young describes a maturity curve that Becca, head of sales at Clay, presented at an event Cassie hosted. Level one is individuals using AI, level two is a centralized view with standardized use, and level three is working out how to create go-to-market alpha. Becca's view, from Clay's work with many sales teams, is that most people are hovering at level one and maybe level two.
“most people are like hovering at number one and like maybe number two”
Deploying AI through one central team, built into the tools reps already use, reduces change-management friction. Listen
Kyle Norton says his company's centralized approach emerged early, when a small group became obsessed with applying AI. They built things and deployed them to reps inside the surfaces they already used rather than asking everyone to learn new tools. He says the central owner need not be one person or an AI tsar and could sit in engineering with applied AI or in RevOps.
“we just built things, deployed it to the reps in the surfaces that they already use”
CROs should take their CFO to lunch to learn where the CFO is being pressed, so they can speak the CFO's language. Listen
Cassie Young calls this her number one hack for CROs. She says many CROs do not understand the P&L or how to tell the story of what is happening, and that they need to understand how the CFO thinks about the function and where the board is pressure-testing the CFO.
“my number one hack for CROs is like you better be taking your CFO to to lunch.”
Listen to the episode Metrics & finance Link to this Report a problem
Cassie Young's bar for every executive is doing basic things in Claude Code and understanding how MCP works, because you cannot sell interoperability you do not understand. Listen
Cassie Young says products now have to connect with customers' tools, and that some portfolio companies are prioritising their Claude integration to meet customers where they are. She says executives should have hooked up tools, built automated use cases, and seen where things get stuck or rate-limited, though not necessarily run their whole life through agents.
“I think that every executive needs to be able to do basic things in Claude Code would be my bar.”
When an AI conversation gets garbled, start a fresh context window, because every earlier message is pulled in to answer each new prompt. Listen
Kyle Norton says he spent 10 to 15 hours building an XDR hiring analysis, and when he got stuck and kept spinning he moved to a new terminal window and started again, which made progress. He explains that every token above in the conversation is pulled into the context window to answer each request.
“Okay, I just I need to start in a fresh context window.”
Outcome cost efficiency compares the cost of an AI agent resolving a ticket with the human cost of resolving it, and the higher it is, the stickier the company. Listen
Cassie Young cites John Gleeson's outcome metrics, which she says are meant to matter for customer success more than legacy SaaS metrics. Her example is an agent costing eight dollars to resolve a ticket against a human cost of $24. She says that even if customers like the product, a low figure means you are kind of doomed.
“the higher the OCE, the better, the stickier the company's going to be”
Listen to the episode Retention & customer success Link to this Report a problem
The core four executive attributes are P&L fluency and command, first team thinking, a pulse on the macro, and a strategic network. Listen
Cassie Young uses this framework to assess every executive. P&L fluency means the full financial picture, including revenue versus cash. First team thinking, drawn from Pat Lencioni, means your most senior peer team comes before your own function. Pulse on the macro means constantly rewriting your playbook as the market changes, and the strategic network is your backfill.
“The first is P&L fluency and command.”
Listen to the episode Leadership & culture Link to this Report a problem
Changing quotas mid-year to address a pipeline shortfall is the opposite of first team thinking; the better move is asking how to help generate pipeline. Listen
Cassie Young describes a portfolio company where marketing generated most leads on a high-velocity cycle, and summer seasonality dried up pipeline in July and August. Reps had no pipeline, so the new head of sales changed all the quotas. She says the better question is what can be done to help generate pipeline before September 15, such as a spiff.
“what can I do to help gas the pipe from sales, right?”
Listen to the episode Sales team, hiring & comp Link to this Report a problem
A CRO plan with little variable pay lets a leader think more holistically, and Kyle Norton thinks it is crazy that many CROs are on 50/50 plans. Listen
Kyle Norton says he has very little variable in his plan, has never missed a quarter, and still focuses intensely on the number. He learned at Shopify, where he had only cash and equity, that this let him make decisions he knew would hurt the sales number but were good for other reasons; he also owned customer onboarding there, which he had to take into consideration.
“I think it's crazy that I know a lot of CROs that are on 50/50 plans.”
Listen to the episode Sales team, hiring & comp Link to this Report a problem
As AI makes work more available, efficient and affordable, demand for that work rises rather than falling. Listen
Cassie Young says history shows that as things become more available and affordable, demand absolutely increases, and that Primary strongly subscribes to this view. Kyle Norton points to software engineering, where more roles are posted than ever and hiring is harder, and says his company ships four times the PRs per engineer as 12 months ago without needing half the engineers.
“as things have become more available, more efficient, right, more affordable, like it absolutely increases demand.”
AI will eliminate administrative middle-management work, such as rolling up forecasts and moving information between systems, while systems thinkers gain value. Listen
Kyle Norton calls it a cliché but a useful frame: if your day is rolling up a forecast, passing information between places, or intaking data to put in a system, those jobs should go away. People who think systematically and orchestrate AI tools can, in his view, see their value go up 10x.
“AI is really going to be the death of the administrator and the rise of the orchestrator”
Listen to the episode Leadership & culture Link to this Report a problem
Letting everyone experiment with AI across many initiatives without clear owners or objectives leaves a company without focus. Listen
Cassie Young says many organisations are trying dozens of AI initiatives without a clear owner or objectives. She compares this to the 2006 Yahoo peanut butter manifesto, where everyone spreads themselves thin across many things.
“one of the downsides of letting everybody experiment, do you know what I mean? Is you just end up without real focus.”
Listen to the episode Strategy & market Link to this Report a problem
At seed, a founder can accept a high burn multiple in year one to build an early-mover advantage, provided there is a plan to bring it down. Listen
Cassie Young says Primary's first check-in is at seed, and it is not uncommon to see crazy-looking burn multiples in year one. Founders may be investing in R&D ahead of commercialization or keeping pace with the roadmap, and she says the context around the number is everything.
“it allows them to establish this early mover advantage, but the operative part of that is they have a plan to bring it down.”
Listen to the episode Metrics & finance Link to this Report a problem